Vacation with the Magic, Disney & Beyond | an Authorized Disney Vacation Planner Agency

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Plan Your Travel With The People Who Know!

BAREFOOT BREAK IN THE BRITISH VIRGIN ISLANDS on Wind Surf

Cruise, Ocean cruise, Small Ship/Yacht
Wind Surf Capri
Exterior view of Wind Surf sailing near Capri, Italy
Photo Credit: Roger Paperno
  • Exterior view of Wind Surf sailing near Capri, Italy - Photo Credit: Roger Paperno
  • Exterior view of Wind Surf
  • Exterior view of Wind Surf - Photo Credit: Jeff Zaruba
  • Close-up exterior view of Wind Surf bow - Photo Credit: Roger Paperno
  • Exterior view of Wind Surf - Photo Credit: Roger Paperno
The British Virgin Islands is known as the yachting capital of the Caribbean and this five-day escape shows you why. Come with us to charming islands with a laid-back attitude, places where you can still find incredible natural beauty, and colonial towns that effortlessly blend Dutch, French, and Caribbean cultures. Explore 17th century forts and duty-free shopping on St. Maarten and St. Bart. Go snorkeling or take a Jeep off-roading on mountainous Tortola. Visit the Baths on Virgin Gorda – a series of granite boulders sculpted by the sea into incredible natural pools and grottoes. And spend the night on Jost Van Dyke, enjoying the island long after the day-trippers leave – your own private paradise with postcard-pretty crescent beaches, quirky beach bars, and the famous effervescent sea water of the Bubbly Pool.
About Wind Surf
About Windstar Cruises
Windstar Cruises logo
THE WORLD'S BEST SMALL SHIP CRUISE LINE

NO ONE ELSE GOES SO FAR TO GET TRAVELERS SO CLOSE …
You’re closer to secluded coves, tiny villages, misty fjords. To ancient ruins, medieval alleyways, quaint marinas. To unspoiled beaches, unfamiliar cultures, undiscovered atolls. To enlivening your curiosity and awakening your sense of wonder. You’re closer than ever to the kind of authentic and unforgettable experiences that you travel to find in the first place. You’re about to board Windstar. And you’re closer to all the places that larger ships can’t reach.

SEE A WORLD FEW WILL EVER SEE …
Welcome to a world of understated elegance and uncommon beauty. A world that leaves crowds and commonplace behind to find unique ports of call, and local, exotic cultures that are at once fascinating and wondrous. A world that’s equal parts intimate, indulgent and inspiring. Where the allure and beauty and magic of the places you sail to is equaled only by the ship that takes you there.

Dec 02, 2025 through
Dec 07, 2025
Nov 26, 2025 7:00 PM
5 Nights from
$1,999.00 (USD)
Per Person
+ $99.00 taxes/fees
Category b

Itinerary

Day Port Arrive Depart
1 Philipsburg, St. Maarten 7:00 PM
2 Jost Van Dyke, Great Harbour 7:00 PM
2 Soper's Hole 8:00 AM 6:00 PM
3 Jost Van Dyke, Great Harbour 10:00 PM
4 Virgin Gorda / Prickly Pear, British Virgin Islands 8:00 AM 5:00 PM
5 Gustavia 8:00 AM 10:00 PM
6 Philipsburg, St. Maarten 6:00 AM
Prices are per-person based on double occupancy, unless otherwise noted.